#------------------------------------------------------------------------------
#$Date: 2020-11-29 04:57:23 +0200 (Sun, 29 Nov 2020) $
#$Revision: 259315 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241577.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7241577
loop_
_publ_author_name
'Lombard, Jean'
'Smith, Vincent J.'
'le Roex, Tanya'
'Haynes, Delia A.'
_publ_section_title
;
 Crystallisation of organic salts by sublimation: salt formation from the
 gas phase
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7826
_journal_page_last               7831
_journal_paper_doi               10.1039/D0CE01470B
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         '2(C10 H8 N2), 2(C2 H2 O4)'
_chemical_formula_sum            'C24 H20 N4 O8'
_chemical_formula_weight         492.44
_chemical_name_common            '4,4-bipyridine oxalic acid'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-17 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                73.741(2)
_cell_angle_beta                 72.890(2)
_cell_angle_gamma                72.483(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7731(5)
_cell_length_b                   9.8652(5)
_cell_length_c                   13.9929(7)
_cell_measurement_reflns_used    7354
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.21
_cell_volume                     1079.17(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics
'X-seed (Barbour, 2001; Atwood & Barbour, 2003)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'charge integrating pixel array detector'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            42048
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_min         2.214
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\ms 3.0'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, 2016/2'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.198
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.0936
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1471P)²+0.6337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2370
_refine_ls_wR_factor_ref         0.2930
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2798
_reflns_number_total             5389
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01470b2.cif
_cod_data_source_block           2b_RT
_cod_original_cell_volume        1079.2(1)
_cod_database_code               7241577
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.977
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2139(3) 0.6025(2) 0.6314(2) 0.0523(7) Uani 1 1 d . . . . .
H1 H -0.283(5) 0.487(5) 0.627(3) 0.094(15) Uiso 1 1 d . . . . .
O2 O 0.0295(3) 0.4437(3) 0.6255(2) 0.0586(7) Uani 1 1 d . . . . .
C3 C -0.0560(4) 0.5643(3) 0.6286(2) 0.0391(7) Uani 1 1 d . . . . .
C4 C 0.0101(4) 0.6916(3) 0.6295(2) 0.0399(7) Uani 1 1 d . . . . .
O5 O -0.0642(3) 0.8156(3) 0.6088(2) 0.0716(9) Uani 1 1 d . . . . .
O6 O 0.1526(3) 0.6495(3) 0.6514(2) 0.0562(7) Uani 1 1 d . . . . .
H6 H 0.184(4) 0.745(4) 0.638(2) 0.053(10) Uiso 1 1 d . . . . .
N7 N 0.2804(3) 0.8582(3) 0.63745(19) 0.0382(6) Uani 1 1 d . . . . .
C8 C 0.4162(4) 0.8232(3) 0.6724(2) 0.0376(7) Uani 1 1 d . . . . .
H8 H 0.456770 0.726757 0.701989 0.045 Uiso 1 1 calc R U . . .
C9 C 0.4981(3) 0.9263(3) 0.6659(2) 0.0345(7) Uani 1 1 d . . . . .
H9 H 0.593195 0.899160 0.690193 0.041 Uiso 1 1 calc R U . . .
C10 C 0.4374(3) 1.0707(3) 0.6228(2) 0.0295(6) Uani 1 1 d . . . . .
C11 C 0.2966(4) 1.1049(3) 0.5856(2) 0.0379(7) Uani 1 1 d . . . . .
H11 H 0.253502 1.200139 0.555029 0.045 Uiso 1 1 calc R U . . .
C12 C 0.2220(4) 0.9961(3) 0.5947(2) 0.0389(7) Uani 1 1 d . . . . .
H12 H 0.127644 1.019543 0.570068 0.047 Uiso 1 1 calc R U . . .
C13 C 0.5209(3) 1.1842(3) 0.6208(2) 0.0322(7) Uani 1 1 d . . . . .
C14 C 0.6855(4) 1.1516(4) 0.6241(2) 0.0418(8) Uani 1 1 d . . . . .
H14 H 0.748733 1.056888 0.625651 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7544(4) 1.2585(4) 0.6250(3) 0.0455(8) Uani 1 1 d . . . . .
H15 H 0.864432 1.234335 0.627337 0.055 Uiso 1 1 calc R U . . .
N16 N 0.6692(3) 1.3961(3) 0.6226(2) 0.0413(7) Uani 1 1 d . . . . .
C17 C 0.5117(4) 1.4297(3) 0.6185(3) 0.0441(8) Uani 1 1 d . . . . .
H17 H 0.452224 1.525555 0.616616 0.053 Uiso 1 1 calc R U . . .
C18 C 0.4326(4) 1.3280(3) 0.6168(2) 0.0393(7) Uani 1 1 d . . . . .
H18 H 0.323080 1.355524 0.613015 0.047 Uiso 1 1 calc R U . . .
O19 O 0.8424(3) 0.5676(2) 0.8844(2) 0.0508(7) Uani 1 1 d . . . . .
H19 H 0.874(8) 0.655(7) 0.881(5) 0.16(3) Uiso 1 1 d . . . . .
H24 H 0.440(7) 0.442(6) 0.876(4) 0.13(2) Uiso 1 1 d . . . . .
O20 O 0.6038(3) 0.7297(2) 0.8783(2) 0.0496(6) Uani 1 1 d . . . . .
C21 C 0.6908(3) 0.6078(3) 0.8797(2) 0.0323(7) Uani 1 1 d . . . . .
C22 C 0.6239(3) 0.4810(3) 0.8760(2) 0.0311(6) Uani 1 1 d . . . . .
O23 O 0.7111(3) 0.3603(2) 0.87441(19) 0.0462(6) Uani 1 1 d . . . . .
O24 O 0.4705(3) 0.5208(2) 0.87398(19) 0.0460(6) Uani 1 1 d . . . . .
N25 N 0.3502(3) 0.3152(3) 0.87138(18) 0.0345(6) Uani 1 1 d . . . . .
C26 C 0.4270(4) 0.1750(3) 0.8901(2) 0.0391(7) Uani 1 1 d . . . . .
H26 H 0.531102 0.149113 0.903199 0.047 Uiso 1 1 calc R U . . .
C27 C 0.3562(3) 0.0669(3) 0.8908(2) 0.0382(7) Uani 1 1 d . . . . .
H27 H 0.413753 -0.029912 0.902899 0.046 Uiso 1 1 calc R U . . .
C28 C 0.1991(3) 0.1021(3) 0.87329(19) 0.0262(6) Uani 1 1 d . . . . .
C29 C 0.1220(3) 0.2494(3) 0.8535(2) 0.0346(7) Uani 1 1 d . . . . .
H29 H 0.017309 0.279178 0.840917 0.042 Uiso 1 1 calc R U . . .
C30 C 0.2020(4) 0.3510(3) 0.8525(2) 0.0385(7) Uani 1 1 d . . . . .
H30 H 0.149549 0.448983 0.838042 0.046 Uiso 1 1 calc R U . . .
C31 C 0.1192(3) -0.0108(3) 0.87593(19) 0.0281(6) Uani 1 1 d . . . . .
C32 C 0.1858(3) -0.1576(3) 0.9091(2) 0.0357(7) Uani 1 1 d . . . . .
H32 H 0.284774 -0.187289 0.929253 0.043 Uiso 1 1 calc R U . . .
C33 C 0.1049(4) -0.2590(3) 0.9119(2) 0.0396(7) Uani 1 1 d . . . . .
H33 H 0.150201 -0.356567 0.935870 0.047 Uiso 1 1 calc R U . . .
N34 N -0.0350(3) -0.2239(3) 0.88203(19) 0.0355(6) Uani 1 1 d . . . . .
C35 C -0.1011(4) -0.0841(3) 0.8498(3) 0.0423(8) Uani 1 1 d . . . . .
H35 H -0.199528 -0.058627 0.829440 0.051 Uiso 1 1 calc R U . . .
C36 C -0.0291(4) 0.0250(3) 0.8454(2) 0.0382(7) Uani 1 1 d . . . . .
H36 H -0.078778 0.121691 0.822316 0.046 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 H1 115.0(17) . . ?
O2 C3 O1 124.6(3) . . ?
O2 C3 C4 122.9(3) . . ?
O1 C3 C4 112.5(3) . . ?
O5 C4 O6 125.3(3) . . ?
O5 C4 C3 121.8(3) . . ?
O6 C4 C3 112.8(3) . . ?
C4 O6 H6 102.0(19) . . ?
C12 N7 C8 119.4(3) . . ?
N7 C8 C9 121.7(3) . . ?
N7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C10 119.5(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 117.9(3) . . ?
C9 C10 C13 119.6(3) . . ?
C11 C10 C13 122.5(3) . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N7 C12 C11 122.2(3) . . ?
N7 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C18 C13 C14 117.6(3) . . ?
C18 C13 C10 119.8(3) . . ?
C14 C13 C10 122.6(3) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N16 C15 C14 122.3(3) . . ?
N16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 N16 C17 118.3(3) . . ?
N16 C17 C18 123.1(3) . . ?
N16 C17 H17 118.5 . . ?
C18 C17 H17 118.5 . . ?
C17 C18 C13 118.5(3) . . ?
C17 C18 H18 120.7 . . ?
C13 C18 H18 120.7 . . ?
C21 O19 H19 106(4) . . ?
O20 C21 O19 126.1(3) . . ?
O20 C21 C22 121.2(3) . . ?
O19 C21 C22 112.7(2) . . ?
O23 C22 O24 125.9(3) . . ?
O23 C22 C21 121.5(3) . . ?
O24 C22 C21 112.5(2) . . ?
C22 O24 H24 107(4) . . ?
C30 N25 C26 118.6(2) . . ?
N25 C26 C27 121.9(3) . . ?
N25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
C26 C27 C28 120.4(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C29 C28 C27 116.5(2) . . ?
C29 C28 C31 121.9(2) . . ?
C27 C28 C31 121.6(3) . . ?
C30 C29 C28 119.6(3) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
N25 C30 C29 123.0(3) . . ?
N25 C30 H30 118.5 . . ?
C29 C30 H30 118.5 . . ?
C32 C31 C36 116.6(3) . . ?
C32 C31 C28 122.0(2) . . ?
C36 C31 C28 121.4(3) . . ?
C33 C32 C31 119.8(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
N34 C33 C32 123.1(3) . . ?
N34 C33 H33 118.5 . . ?
C32 C33 H33 118.5 . . ?
C33 N34 C35 118.2(3) . . ?
N34 C35 C36 122.5(3) . . ?
N34 C35 H35 118.7 . . ?
C36 C35 H35 118.7 . . ?
C35 C36 C31 119.7(3) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.313(3) . ?
O1 H1 1.46(5) . ?
O2 C3 1.205(4) . ?
C3 C4 1.538(4) . ?
C4 O5 1.200(4) . ?
C4 O6 1.292(4) . ?
O6 H6 1.01(4) . ?
N7 C12 1.332(4) . ?
N7 C8 1.333(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(4) . ?
C10 C13 1.502(4) . ?
C11 C12 1.377(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.391(4) . ?
C13 C14 1.393(4) . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 N16 1.335(4) . ?
C15 H15 0.9300 . ?
N16 C17 1.336(4) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
O19 C21 1.285(3) . ?
O19 H19 0.97(7) . ?
O20 C21 1.213(3) . ?
C21 C22 1.552(4) . ?
C22 O23 1.209(3) . ?
C22 O24 1.290(3) . ?
O24 H24 0.88(6) . ?
N25 C30 1.326(4) . ?
N25 C26 1.332(4) . ?
C26 C27 1.384(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.394(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.392(4) . ?
C28 C31 1.471(4) . ?
C29 C30 1.382(4) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.388(4) . ?
C31 C36 1.402(4) . ?
C32 C33 1.377(4) . ?
C32 H32 0.9300 . ?
C33 N34 1.328(4) . ?
C33 H33 0.9300 . ?
N34 C35 1.329(4) . ?
C35 C36 1.381(4) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O6 H6 N7 1.01(4) 1.59(4) 2.563(3) 160(3) . yes
O19 H19 N34 0.97(7) 1.63(7) 2.581(3) 166(6) 1_665 yes
O24 H24 N25 0.88(6) 1.70(6) 2.566(3) 168(6) . yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 O5 162.3(4) . . . . ?
O1 C3 C4 O5 -17.7(5) . . . . ?
O2 C3 C4 O6 -15.7(5) . . . . ?
O1 C3 C4 O6 164.3(3) . . . . ?
C12 N7 C8 C9 0.3(5) . . . . ?
N7 C8 C9 C10 0.6(5) . . . . ?
C8 C9 C10 C11 -1.3(4) . . . . ?
C8 C9 C10 C13 176.7(3) . . . . ?
C9 C10 C11 C12 1.2(4) . . . . ?
C13 C10 C11 C12 -176.7(3) . . . . ?
C8 N7 C12 C11 -0.4(5) . . . . ?
C10 C11 C12 N7 -0.4(5) . . . . ?
C9 C10 C13 C18 -154.7(3) . . . . ?
C11 C10 C13 C18 23.2(4) . . . . ?
C9 C10 C13 C14 24.5(4) . . . . ?
C11 C10 C13 C14 -157.6(3) . . . . ?
C18 C13 C14 C15 1.1(5) . . . . ?
C10 C13 C14 C15 -178.1(3) . . . . ?
C13 C14 C15 N16 -0.1(5) . . . . ?
C14 C15 N16 C17 -0.5(5) . . . . ?
C15 N16 C17 C18 0.2(5) . . . . ?
N16 C17 C18 C13 0.8(5) . . . . ?
C14 C13 C18 C17 -1.3(5) . . . . ?
C10 C13 C18 C17 177.9(3) . . . . ?
O20 C21 C22 O23 177.9(3) . . . . ?
O19 C21 C22 O23 -2.3(4) . . . . ?
O20 C21 C22 O24 -1.6(4) . . . . ?
O19 C21 C22 O24 178.3(2) . . . . ?
C30 N25 C26 C27 -0.2(5) . . . . ?
N25 C26 C27 C28 -1.2(5) . . . . ?
C26 C27 C28 C29 1.4(4) . . . . ?
C26 C27 C28 C31 -178.5(3) . . . . ?
C27 C28 C29 C30 -0.3(4) . . . . ?
C31 C28 C29 C30 179.6(3) . . . . ?
C26 N25 C30 C29 1.3(5) . . . . ?
C28 C29 C30 N25 -1.1(5) . . . . ?
C29 C28 C31 C32 -171.1(3) . . . . ?
C27 C28 C31 C32 8.8(4) . . . . ?
C29 C28 C31 C36 8.5(4) . . . . ?
C27 C28 C31 C36 -171.6(3) . . . . ?
C36 C31 C32 C33 -0.9(4) . . . . ?
C28 C31 C32 C33 178.8(3) . . . . ?
C31 C32 C33 N34 1.5(5) . . . . ?
C32 C33 N34 C35 -1.4(5) . . . . ?
C33 N34 C35 C36 0.7(5) . . . . ?
N34 C35 C36 C31 -0.1(5) . . . . ?
C32 C31 C36 C35 0.2(4) . . . . ?
C28 C31 C36 C35 -179.4(3) . . . . ?
